Reacción #66058

ord-a5fea26026064afdac0acd6239aa65d2

Ecuación de reacción

CCCOS(=O)(=O)c1ccc(C)cc1
propyl tosylate
Cc1ccc(S(=O)(=O)O)cc1
P-TSA

Condiciones de reacción

Temperatura
65°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroA 12 L, three necked flask was equipped with an overhead stirrer
  2. 2
    workup.ADDITIONa temperature probe, a heating mantle, a claisen joint, a condenser, and a 500 ml addition funnel
  3. 3
    workup.ADDITIONThis solution was added to the 12 L flask dropwise over a period of 2.0 hours

Procedimiento

A 12 L, three necked flask was equipped with an overhead stirrer, a temperature probe, a heating mantle, a claisen joint, a condenser, and a 500 ml addition funnel. The flask was charged with 250 grams of R(+)-2,6 diamino-4,5,6,7-tetrahydro-benzothiazole (R(+) diamine), followed by 2 L of dimethyl formamide (DMF). Under continuous stirring, the mixture was heated to a temperature of 65° C. The addition funnel was charged with a solution of 386.6 grams propyl tosylate (1.25 molar equivalents) and 322 ml diisopropylethyleamine (1.25 molar equivalents) in 500 ml DMF. This solution was added to the 12 L flask dropwise over a period of 2.0 hours. The reaction was monitored by analysis on HPLC.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08524695B2uspto-grants-2013_09